(8 minute read)
By their nature, career transitions tend to involve a lot of self-centered thinking. What do I want to do with my life? What will make me feel fulfilled? These are important questions, but, they only solve part of the problem. There’s always a stakeholder on the other side who must agree to take on the risk that comes with fulfilling the career transitioner’s goals. The vast majority of time that person is a hiring manager.
This post provides a framework to describe how hiring managers think about taking on the risk that comes with employing a career transitoner. To illustrate, let’s start with a story:
Michelle, has finally had it with her job. She’s ready to leave, and even knows what kind of job she wants next. Like many people, Michelle logs onto Indeed or AngelList to start searching for open positions. She lobs out a few applications and waits for the responses to roll in.
What factors determine whether her applications turn into phone screens, or, if those phone screens turn into on-sites, and ultimately a new job?
The deciding factor is how much hiring risk she’s asking employers to take on. This type of risk can be seen in several ways:
- Financial – the company must pay to hire, relocate, train and compensate Michelle. If things don’t work out, there’s also the additional cost of severance and potential litigation.
- Time – employees will need to spend time hiring and training her. If she performs poorly, the team’s performance will also get dragged down by the ensuing drama.
- Social – If Michelle gets fired, those who vouched for her will see their credibility damaged. And, if she turns out to be really toxic, other employees may leave to avoid having to work with her.
While the whole company shares in this risk, it’s the hiring manager who bears the largest share of it. A manager’s performance is judged by the output of his team. For the reasons above a bad hire can drag down the performance of a whole team. Since a poorly performing team can limit the manager’s career growth within the company, hiring managers tend to be naturally risk averse when bringing on new people.
Since it’s hard to know if a new hire will work out, most hiring managers try to cover their asses by hiring candidates with obvious signals of legitimacy. In the case a hire doesn’t work out, the hiring manager say, “well, who’d have thought that someone who worked at Google would have been such a bad fit here?” In the vein of the oft-cited saying that “no one ever got fired for buying IBM,” no one ever got fired for hiring from Google.
There are several different attributes that contribute to hiring risk, including:
- Functional risk– does the candidate have the ability to accomplish the objectives of this role?
- Stage risk – does the candidate have experience operating in a work environment like this one?
- Culture risk – will the candidate’s values, attitudes, and habits mix well with the other people on this team?
- Customer risk – does the candidate have experience solving problems or creating solutions for our customer?
- Problem risk – has the candidate created solutions to solve this type of problem before?
- Solution risk – how comfortable is the candidate with the process of building and selling this type of solution?
The amount of hiring risk a candidate is asking a manager to take on is roughly equivalent to the riskiness of a candidate’s career transition. In other words, the more things Michelle tries to change from one job to the next, the more transition risk she’s taking on.
What to do about it
To deal with this risk you basically have two levers at your disposal:
- Offer more
- Ask for less
Offering more means you’re either expanding the abilities you can share with your employer or the time you can devote to work. In my experience, most transitioners tend to understand the value of this lever. They believe that by spending enough time building skills, or demonstrating how much time they will dedicate to the job, employers will give them a shot. While I, of course, believe this is an essential part of accomplishing any career transition I think it’s lever #2 that gives transitoners a better chance at overcoming hiring risk.
The catch 22 of any career transition is that hiring managers want to see that you have experience doing the job, but to get that experience you need a job that offers experience. So how can you convince an employer to give you a shot?
Ask for less.
In practice, this means making a smaller ask from the gatekeeper that’s standing in the way of you getting the experience you want. Once you’ve had the experience, you can then ask for slightly more. I think of this as climbing the ladder of legitimacy.
To illustrate, let’s return to Michelle. She’s an architect with dreams of landing a product design role at Slack. In her current role she represents almost every type of risk to her future hiring manager at Slack. She has no experience with Slack’s customer, problem, or solution. Furthermore, her architecture firm is significantly smaller, has grown much slower, and probably has a very different culture. What Michelle does have going for her is a functional skillset that shares a lot of similarities with digital product design.
Assuming Michelle has the intellect and motivation to build the skills she needs, let’s look at how she might climb the ladder of legitimacy to assuage her future hiring manager’s fears.
Rung #1: Contribute to or observe a project for free
This allows Michelle to get her hands dirty with digital product design while mitigating the risk of her involvement by involving more experienced people and not asking for money. While it may seem like a small ask to contribute to a project for free, she’s asking both the other contributors and the client to entrust her with sensitive information and their time.
Rung #2: Lead or play a major role on a project for free
To get here she’ll need to demonstrate that she can make the rest of the team look good by delivering a quality work product in a timely manner. In selecting which projects to work on, she may want to consider projects at companies that are similar to Slack.
Rung #3: Get paid for project work
This will likely be the hardest step of Michelle’s ladder. A few common ways to overcome the challenge of this step:
- Tell clients they only have to pay if they find the work valuable or offer a money-back guarantee
- Ask for a low rate
- Keep the project scope small
- Bring other members on the team with more legitimacy
Rung #4: Find a short-term contract with a client
She’s now asking to not only to get paid, but for more serious responsibility in return for ongoing payment. Of course the contract is limited so the client doesn’t need to fear giving her severance, if things don’t work. If she’s having trouble getting traction at this step, she can always offer her time and abilities for a lower hourly rate. Again, this will be a great opportunity to look for a company with some similarities to Slack.
Rung #5: Get a full-time role in the right function
While this may seem like the top rung of the ladder, Michelle may still be a ways off from her ideal role at Slack. Often, in order to get a company comfortable with making a full-time offer, it’s necessary to take a chance on a small company that no one has heard of or a larger company that’s lost its luster. For those who are able, I think it’s much better in the long run to compromise on taking a lower salary in exchange for a manager or team with more promise.
Rung #6: Land the dream job
Assuming Michelle has kicked ass at her last company, and has gained some relevant experience to match what she wants to do with Slack, she’s now in a much better position to put her hiring manager’s mind at ease.
Keep in mind, that for companies that are really hot (let’s say Slack in 2016, or a company like Opendoor today) she may be looking at a few more rungs between #5 and #6, but the same principles still hold.
In summary, here’s how I view the steps to accomplishing a career transition:
- Figure out your goal
- Develop an understanding of how much risk you’re asking an employer to take on
- Fill in the necessary skill gaps to make a contribution
- Gain experience by contributing your abilities, and asking little in return
- Find ways to represent the contributions you’ve made to future gatekeepers
- Repeat steps 3-5 by contributing in increasingly more meaningful ways, accompanied by slightly larger asks
And, of course, if you, or someone you care about, is going through a transition, don’t hesitate to reach out.